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Patented Dec. 19, 1922.

MORTIMER BYE AND LEWIS H. DETROIT, MICHIGAN, ASSIGNOR-S FREDERICK STEARNS &'CO1lllIPAI'\l"S T, (l1? DETRQIT, MICHIGAN, CORPORATION .MIGHIGAN.

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MEDICINAL rnnrnni-xrrron.

No Drawing. Application filed June 6,

To all whom it may concern:

Be it known that we, Monrmrnn BYE and Lnwrs H. CARLSON, citizens of the United States, residing at Detroit, in the county of l/Vayne and State of Michigan, have invent ed certain new and useful Improvements in Medicinal Preparations, of which the following is a specification.

As is well known, the muscles of the body are divided into two general classes commonly referred to as striped and unstriped muscles. The unstriped or smooth are the involuntary muscles of the body, that is, those that are not ordinarily controlled by the will but operate automatically. Heretofore the pain or spasm of such muscles has been controlled or relieved chiefly by the administration of narcotics, which tend to seriously affect the vital functions of the body and frequently lead to the formation of habits of drugadditions. The object of our said invention is to provide a medicinal agent for the treatment of pain or spasm caused directly or indirectly by the unstriped or smooth or involuntary muscles which will. be very eflicient in its action, harmless in results, and without objectionable characteristics in its ad ministration.

Such medicinal agent consists of a white, practically tasteless and odorless crystalline powder made by the action of benzyl alcohol on succinic acid, resulting; in benzyl sue cinate of the formula UH 2C0 O Clin cs 5 or C1|H1a04 ciucoomnc n5 Said product is manufactured by the following process: We take, for example, 1600 grams of .succiuic acid and mix with 2700 cc. of hennvl alcohol in a 5 liler. round bot" tom, pyrex desk and connect the flash with a reflux; condenser and pla e the flash in an. oil bath. This bath. is then heated to 185 to 1 5 (l. The first bubbling appears at about 160" (l. and at 180 to 185 C. there appears a lively boiling. The heat is maintained at 185 to 195 (l. for about eight hours. It is then allowed to cool when there will be found a deposit of unreacted sue cinic acid which is then filteredofl'. The filtrate is now subjected to a vacuum distillation. The material which remains in the flask above 200 C. at 15 mm. pressure is saved, The material in the receiving flask:

1921. Serial No. 475,500.

contains water, unreacted benzyl alcohol, and succinic acid. Thus far the process has not been unknown but has not been used for practical purposes, and does not result in a purified 0r practical medicinal product for such purposes as ours is intended to be used for. vAt this point we transfer the material from the flask to a 1,000 cc. beaker and 5 per cent or more of its volume of a foreign solvent such as alcohol or other appropriate solvent is added. It is then al lowed to freeze by placing the beaker in an ice bath. It is then stirred and the benzyl succinate will crystallize out. The material in the beaker will become a mass of crystals. It is then filtered by suction or pressure and the benzyl succinate allowed to dry in the open. After the bcnzyl succinate is dried in the open, it becomes necessary to recrystallize again from alcohol. or other appropriate solvent. This process with the materials stated will produce a yield of about 1620 grams of benzyl succinate,

It will be itinderstood, of course, that the process described may be modified in any manner that may be found practicable to produce the described product, the process here outlined being; one that we have practiced and found entirely suitable for the purpose.

Having thus fully described our said invention, what we claim as new and desire to secure by Letters Patent, is:

l. The method of prodijicing bcuzyl sue cinate in the form of crystalline powder which consists in treating succinic acid with benzyl alcohol, heating the same, then filtering, then adding a foreign solvent, then freezing", then drying.

2. The method of producing bony/y] succiuatc in the form of crystalline powder which i-ljmsists in treat-inn; sur inic acid with benarl alcohol, heating the same, then filtering-3f, then distilling by vacuum, then adc 'ng a foreign sol vent, then crystallining by freer inn, then filtering, then drying. then re cryslalliziug, and then. d rying.

3. The method of producing a mcdiciiml agent in the form of crystalline powder which consists in treating succinic acid with benzyl alcohol and then reducing to the form of powder by a method which includes concentration and then dilution in a foreign solvent crystallization by freezing, substantially as set forth.

41. The method. of producing a medicinal 1n Witness whereof, weshzwe hereunto set 10 agent in the form of crystalline powder our hands and. seals at Detroit, Michigan, Wl'llCll consists 1n treating sueelnlc and with this 4th day of June, A. D. nineteen hunbenzyl alcohol and reducing to the form 01' dred and twenty-one.

first heating, and then diluting by the addi- MORTIMER BYE. Li s.]

dry powder by A method which includes V,

LEWIS H. CARLSON, [14, s.]

tion of a foreign solvent, then crystallizing Witnesses: by freezing, and then drying, substantially E. BERENDES, as set forth. G.- A; SAUER. 

